Fun Things to Do in Chicago: A Windy City Bucket List

Whether you’re a first-time visitor to Chicago or a Windy City connoisseur, add these 10 fun things to your Chicago must-see list. Book your vacation rental home in Chicago to create a home base that feels like home before you head out to see the sights.

Here’s what to do in Chicago

Wander the Hallowed Halls of the Art Institute of ChicagoDom1530/Shutterstock.com

From European armor to Impressionist paintings, the museum provides art education that includes over 300,000 works. Spend a few hours wandering through the museum and view the permanent displays of Renoir and Vincent van Gogh.

Catch a Game at Wrigley FieldDan Kosmayer/Shutterstock.com

Wrigley Field is a must-see for both baseball fanatics and anyone who loves a great hot dog. As the second-oldest baseball park in the United States, Wrigley Field has been a Chicago institution since 1914. Delicious dogs, green beer on St. Paddy’s Day and a chance at watching history being made give Wrigley Field its aura of excitement.

Visit the Field Museum for Natural HistoryLocated on the Grant Park’s Museum Campus, the Field Museum provides history lovers with everything from Egyptian mummies to interactive dinosaur exhibits. Meet “Sue” the T. rex, or take in a lecture in the Abbott Hall of Conservation.

Spend Some Cash on the Magnificent MileDibrova/Shutterstock.com

This stretch of shops, restaurants and homes between the Chicago River and Lake Shore Drive beckons to anyone with an eye for fashion and a taste for delicious food. The holiday season gives vacationers an added bonus by ramping up store window displays to create a festive shopping experience.

Share Your Love of the Ocean at the Shedd AquariumWander the halls of one of the top aquariums in the United States and make friends with over 32,000 sea creatures. With everything from beluga whales to sharks and playful penguins, this Chicago staple is on everyone’s bucket list.

Take in the Cityscape at the 360 Chicago Observation DeckTowering 1,000 feet over the heart of downtown Chicago, the 360 Chicago Observation Deck greets guests with breathtaking views of the city. Pick a clear day, and you can see over 50 miles in any direction.

Watch the Fur Fly at the Lincoln Park ZooFelix Mizioznikov/Shutterstock.com

With animals ranging from flying foxes to icy polar bears, the Lincoln Park Zoo does not disappoint animal lovers with its huge variety of land, sea and air creatures. No entrance fee means this bucket list item is also a budget bargain.

Breathe in the Fantastic Fragrances of Maggie Daley ParkAcres of green and gardens create a feast-for-the-senses outdoor space at Maggie Daley Park. Take an hour or two to enjoy the blossoms, and check out the city views.

Explore the Exhibits at the Museum of Science and IndustryS White/Shutterstock.com

With over 32,000 artifacts on display, the Chicago Museum of Science and Industry encompasses the entire Palace of Fine Arts. The building itself is a wonder, covering over 14 a10. cres.

Take in the Chicago Architecture River CruiseGreen or not, the Chicago River winds its way through some of the most historic portions of the Windy City. A 90-minute river cruise takes you from the Navy Pier through the Magnificent Mile while focusing on the beauty of Chicago’s unique architecture.

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